Here are some of the best questions for a Free Trial Users survey about onboarding experience, plus tips on how to create them. If you want to build a great survey in seconds, Specific can help you generate conversational surveys using AI.
Best open-ended questions for Free Trial Users survey about onboarding experience
If you want actionable insights from your Free Trial Users, open-ended questions are a must. They let people share details in their own words—especially valuable when you’re exploring new onboarding flows or want to dig beneath the surface of what works and what doesn’t. Open-ends give users the freedom to highlight what actually mattered to them, versus just picking from a list you anticipated. When you need depth, trends, and stories, start with open questions.
10 open-ended questions to ask Free Trial Users about their onboarding experience:
What was your very first impression when you started using the product?
Was there anything confusing or unclear during the signup process?
How did you feel about the guidance (tutorials, tips, or walk-throughs) provided during onboarding?
What did you expect from the onboarding experience, and did it match reality?
Were there any moments where you felt stuck or overwhelmed?
Which part of the onboarding process was most helpful to you, and why?
What could have made your first session with the product easier or more enjoyable?
Can you describe a specific moment that made you decide to keep using (or stop using) the product?
If you recommended our product to a friend, what would you tell them about the onboarding?
Is there one thing you wish we’d asked or shown you during onboarding that we didn’t?
Open questions like these often surface pain points or unmet needs you might not have anticipated. Considering 81% of new hires report feeling overwhelmed with information during onboarding, it’s vital to allow users to describe in their own words what helped or hindered them. [1]
Best single-select multiple-choice questions for Free Trial Users survey about onboarding experience
Single-select multiple-choice questions shine when you need structured data, want quick benchmarking, or if you’re breaking the ice. They’re great for quantifying issue frequency, measuring perception, or starting a conversation—sometimes it’s easier for someone to click a box than compose a sentence. You can always follow up for details afterward.
Question: How would you rate the clarity of our onboarding instructions?
Very clear
Somewhat clear
Not clear at all
Question: Did you complete all of the steps in the onboarding process?
Yes, all steps
Some, but not all
No, I stopped early
Question: What was the biggest barrier during onboarding?
Too much information
Unclear instructions
Technical issues
Other
When to follow up with "why?" If a user picks “Not clear at all” or “Stopped early,” ask "why?" right after. This turns a blunt stat into valuable feedback. Often, the reason behind a choice will unlock the insight you need to improve the process.
When and why to add the "Other" choice? Use "Other" on lists to let users surface things you didn’t think of—especially for blockers or pain points. A great follow-up to "Other" responses can uncover unexpected, yet critical, issues in your onboarding.
It’s smart to remember that 81% of new hires feel overwhelmed during onboarding, so keeping questions easy—and offering quick choices—reduces friction for busy trial users. [1]
Should you use an NPS question in onboarding feedback surveys?
NPS, or Net Promoter Score, is a classic for understanding loyalty—would someone recommend your product to others? For free trial users in particular, asking an NPS question after onboarding gives you an early pulse: Are users excited enough to invite others, or are they still on the fence?
A typical NPS question looks like this:
On a scale of 0–10, how likely are you to recommend [Product] to a friend or colleague after your onboarding experience?
Depending on their score, it’s standard to follow up: “What’s the primary reason for your score?” This pairs quant data with context.
Want to see this in action? Try generating an NPS survey for free trial users here.
Remember, structured onboarding boosts both retention and satisfaction: 69% of employees are more likely to stay if onboarding is great, while organizations with strong onboarding processes see new hire retention improve by 82%. [2][3]
The power of follow-up questions
Follow-up questions are the secret weapon of conversational surveys. If you’ve ever read a respondent’s answer and thought, “I wish they told me more,” you know why! Automated probing allows us to get beneath quick yes/no or vague “it was fine” replies. You can read more on how automated follow-up questions work in Specific’s automated follow-up questions feature overview.
Free trial user: "The instructions were fine."
AI follow-up: "Could you share a specific moment where the instructions helped you—or where you needed more detail?"
That extra “nudge” can turn surface-level feedback into actionable insight—without endless back-and-forth.
How many followups to ask? Usually, 2–3 follow-ups per open question are plenty. You want enough depth to clarify—but not to exhaust your user. Specific lets you limit follow-up depth and set AI to move on once key answers land. This maintains a natural chat flow.
This makes it a conversational survey: Instead of a static form, your survey becomes a back-and-forth discovery—everyone feels heard.
Easy AI analysis, no stress: Even with all that unstructured text, Specific’s AI-powered analysis makes understanding feedback a breeze. Check out our article on analyzing survey responses with AI to learn more.
With these new AI-powered follow-ups, you’ll never have to chase down clarifications by email again. We encourage you to build a survey with Specific to experience the difference first hand.
How to prompt ChatGPT (or other GPTs) to generate great onboarding questions
If you want to brainstorm survey questions with generative AI, a simple prompt like below will get you started:
Suggest 10 open-ended questions for Free Trial Users survey about onboarding experience.
However, AI works best if you provide as much context as possible. For example, explain who you are, your goals, type of product, and specific concerns. Here’s an enhanced prompt:
We’re a SaaS company with a two-week free trial. Our users run small businesses and often juggle multiple tools. Suggest 10 open-ended questions to reveal pain points and suggestions during onboarding.
Next step: Have the AI organize these questions for clarity and structure. Try:
Look at the questions and categorize them. Output categories with the questions under them.
Then, review suggested categories, choose those that align with your priorities (like "confusion points", "product value", etc.), and ask:
Generate 10 questions for categories product value and onboarding confusion.
This method leads to focused, actionable question sets you can quickly validate and deploy in Specific’s AI survey maker.
What is a conversational survey?
Conversational surveys are a new breed: Instead of a static form, your questions unfold in a natural chat. Respondents feel like they’re talking to a person, not just ticking boxes. The flow adapts to their answers, asking deeper questions in real time—just as a curious, expert interviewer would.
Why does this matter? Because genuine conversations increase engagement and deliver much richer context. You avoid survey fatigue, boost completion rates, and get data that’s far more meaningful than flat forms. This is where AI survey generation is radically better than slow, manual survey creation.
Manual Surveys | AI-Generated Surveys |
|---|---|
Static, fixed set of questions | Adaptive, dynamic, and personalized |
Time-intensive to create and edit | Created and iterated instantly via AI prompts |
No real-time clarifications | Real-time, natural follow-up questions |
Hard to analyze unstructured responses | AI summarizes and themes responses for you |
Why use AI for free trial user surveys? For onboarding, speed matters. With AI-generated conversational surveys, you launch fast, iteratively improve, and automatically analyze results—while making the process enjoyable for users. Want to try this workflow? See our step-by-step guide to creating a free trial onboarding survey.
We built Specific to deliver the smoothest, most engaging experience for both you and your users. If you need best practices, templates, or expert-designed prompts, you’re in the right place—our tools put AI at your fingertips.
See this onboarding experience survey example now
See how a conversational survey powered by AI can instantly level up your onboarding feedback—unlock actionable insights and create a better first impression for every new user. Create your own survey today and discover the difference.